Preparation and Characterization of Urushiol Methylene Acetal Derivatives with Various Degrees of Unsaturation in Alkyl Side Chain

Wang, Chengzhang; He, Yuanfeng; Zhou, Hao; Tao, Ran; Chen, Hongxia; Ye, Jianzhong; Zhang, Yusi

doi:10.1155/2015/843290

Cited by 3 publications

(2 citation statements)

References 16 publications

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“…Xu et al used a water-assisted assembly method to produce urushiol-formaldehyde polymer (UFP) membranes that had a porous structure—and thus good hydrophobic properties and acid and alkali resistance [ 10 ]. Wang et al conducted the interaction between urushiol and methylene chloride in order to synthesize urushiol methylene acetal derivatives which produced valuable leading compounds and further improved the design and development of more effective anticancer agents [ 11 ]. Kim et al used urushiol of RL to synthesize a series of poly (methyl methacrylate)-urushiol polymer composition which were then made into membranes with better thermal stability, highly effective antibacterial and antifouling capacity [ 7 ].…”

Section: Introductionmentioning

confidence: 99%

A Study on the Improvement of Using Raw Lacquer and Electrospinning on Properties of PVP Nanofilms

Zhang

Liu

et al. 2020

Nanomaterials

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Raw lacquer (RL), ethanol being used as the solvent, was added to polyvinyl pyrrolidone (PVP) and then electrospun into RL/PVP nanofilms. Manufacturing parameters such as RL/PVP ratio, voltage, flow velocity, needle type, and the distance between syringe and the collection board were systematically investigated. A scanning electronic microscope (SEM) was used to observe the surface morphology of nanofilms; the block drop method was used to measure the water contact angle; the mechanical properties of RL/PVP nanofilms of different proportions were tested by universal material testing machine; and Fourier-transform infrared spectroscopy (FT-IR) was used to characterize the structure. Based on the water resistance and acid resistance measurements, the proposed nanofilms demonstrated to be water and acid resistant were successfully produced. The results show that PVP that melts in water becomes incompatible with water after adding raw lacquer, and the acid resistance is greatly improved. Furthermore, the smaller the fiber diameter, the better the mechanical properties of the nanofilms are under low ratio of RL/PVP. With a high proportion of RL/PVP, the inner structure of the nanofilm is denser, and the water resistance and acid resistance are better. The dense structure can protect the inner material of the nanofilms.

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Section: Introductionmentioning

confidence: 99%

A Study on the Improvement of Using Raw Lacquer and Electrospinning on Properties of PVP Nanofilms

Zhang

Liu

et al. 2020

Nanomaterials

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“…In addition, urushiol has poor tumor selectivity and biocompatibility, constraining its therapeutic utility and significantly increasing the risk of adverse side effects following its administration. 16 The incorporation of urushiol into pH-sensitive nanoparticles, such as polymeric micelles, has the potential to overcome these limitations by improving the stability and water solubility of this compound while allowing it to be released in a controlled manner at tumor sites in vivo. Such an approach would significantly enhance the biodistribution and pharmacokinetic profile of urushiol in a desirable manner, thus substantially increasing its clinical utility.…”

Section: Introductionmentioning

confidence: 99%

<p>Novel pH-Sensitive Urushiol-Loaded Polymeric Micelles for Enhanced Anticancer Activity</p>

Zhou

Qi²,

Xue

et al. 2020

IJN

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The aim of this study was to develop a means of improving the bioavailability and anticancer activity of urushiol by developing an urushiol-loaded novel tumor-targeted micelle delivery system based on amphiphilic block copolymer poly(ethylene glycol)b-poly-(β-amino ester) (mPEG-PBAE). Materials and Methods: We synthesized four different mPEG-PBAE copolymers using mPEG-NH 2 with different molecular weights or hydrophobicity levels. Of these, we selected the mPEG 5000-PBAE-C 12 polymer and used it to develop an optimized means of preparing urushiol-loaded micelles. Response surface methodology was used to optimize this formulation process. The micellar properties, including particle size, pH sensitivity, drug release dynamics, and critical micelle concentrations, were characterized. We further used the MCF-7 human breast cancer cell line to explore the cytotoxicity of these micelles in vitro and assessed their pharmacokinetics, tissue distribution, and antitumor activity in vivo. Results: The resulting micelles had a mean particle size of 160.1 nm, a DL value of 23.45%, and an EE value of 80.68%. These micelles were found to release their contents in a pH-sensitive manner in vitro, with drug release being significantly accelerated at pH 5.0 (98.74% in 72 h) without any associated burst release. We found that urushiol-loaded micelles were significantly better at inducing MCF-7 cell cytotoxicity compared with free urushiol, with an IC 50 of 1.21 mg/ L. When these micelles were administered to tumor model animals in vivo, pharmacokinetic analysis revealed that the total AUC and MRT of these micelles were 2.28-and 2.53-fold higher than that of free urushiol, respectively. Tissue distribution analyses further revealed these micelles to mediate significantly enhanced tumor urushiol accumulation. Conclusion: The pH-responsive urushiol-loaded micelles described in this study may be ideally suited for clinical use for the treatment of breast cancer.

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Novel urushiol derivatives as HDAC8 inhibitors: rational design, virtual screening, molecular docking and molecular dynamics studies

Zhou

Wang

Deng

et al. 2017

Journal of Biomolecular Structure and Dynamics

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Three series of novel urushiol derivatives were designed by introducing a hydroxamic acid moiety into the tail of an alkyl side chain and substituents with differing electronic properties or steric bulk onto the benzene ring and alkyl side chain. The compounds' binding affinity toward HDAC8 was screened by Glide docking. The highest-scoring compounds were processed further with molecular docking, MD simulations, and binding free energy studies to analyze the binding modes and mechanisms. Ten compounds had Glide scores of -8.2 to -10.2, which revealed that introducing hydroxy, carbonyl, amino, or methyl ether groups into the alkyl side chain or addition of -F, -Cl, sulfonamide, benzamido, amino, or hydroxy substituents on the benzene ring could significantly increase binding affinity. Molecular docking studies revealed that zinc ion coordination, hydrogen bonding, and hydrophobic interactions contributed to the high calculated binding affinities of these compounds toward HDAC8. MD simulations and binding free energy studies showed that all complexes possessed good stability, as characterized by low RMSDs, low RMSFs of residues, moderate hydrogen bonding and zinc ion coordination and low values of binding free energies. Hie147, Tyr121, Phe175, Hip110, Phe119, Tyr273, Lys21, Gly118, Gln230, Leu122, Gly269, and Gly107 contributed favorably to the binding; and Van der Waals and electrostatic interactions provided major contributions to the stability of these complexes. These results show the potential of urushiol derivatives as HDAC8 binding lead compounds, which have great therapeutic potential in the treatment of various malignancies, neurological disorders, and human parasitic diseases.

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Preparation and Characterization of Urushiol Methylene Acetal Derivatives with Various Degrees of Unsaturation in Alkyl Side Chain

Cited by 3 publications

References 16 publications

A Study on the Improvement of Using Raw Lacquer and Electrospinning on Properties of PVP Nanofilms

A Study on the Improvement of Using Raw Lacquer and Electrospinning on Properties of PVP Nanofilms

<p>Novel pH-Sensitive Urushiol-Loaded Polymeric Micelles for Enhanced Anticancer Activity</p>

Novel urushiol derivatives as HDAC8 inhibitors: rational design, virtual screening, molecular docking and molecular dynamics studies

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